I cut my teeth on film too. That makes you think before taking a picture because everyone counts. The same principles apply with digital but you can bang away and experiment without breaking the bank.
I have all the DSLR kit but these days do most of my photography on my phone, it has more features and sophistication than any of my film cameras ever had. When I use the DSLR it is invariably set to an auto mode and I use my judgement to over ride it if I think the results could be better.
The biggest pain with watch photography is controlling reflections caused by domed crystals, I have tried polarising filters but with limited success. I also prefer to capture the perfect picture (no such thing) in camera rather than using photoshop.